Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

22. Carboxylic Acid Derivatives: NAS

Carboxylation

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylation

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2:47 minutes

Problem 39a

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.
(a) PhCH₂CH₂OH → PhCH₂CH₂COOH

Verified step by step guidance

Step 1: Begin by oxidizing the primary alcohol group (-CH2OH) in PhCH2CH2OH to an aldehyde (-CHO). This can be achieved using a mild oxidizing agent such as PCC (Pyridinium Chlorochromate) in an anhydrous solvent like dichloromethane (CH2Cl2). The intermediate product will be PhCH2CH2CHO.

Step 2: Next, oxidize the aldehyde (-CHO) group in PhCH2CH2CHO to a carboxylic acid (-COOH). This can be accomplished using a stronger oxidizing agent such as KMnO4 (Potassium Permanganate) or Jones reagent (CrO3/H2SO4). The product will be PhCH2CH2COOH.

Step 3: Ensure proper reaction conditions for each step. For the PCC oxidation, maintain an anhydrous environment to prevent overoxidation. For the aldehyde oxidation, use aqueous KMnO4 under acidic or neutral conditions to achieve the desired carboxylic acid.

Step 4: Purify the final product (PhCH2CH2COOH) using techniques such as recrystallization or extraction, depending on the solubility and physical properties of the compound.

Step 5: Confirm the structure of the final product using spectroscopic methods such as IR (to verify the presence of the carboxylic acid group), NMR (to confirm the structure of the molecule), and possibly mass spectrometry for molecular weight determination.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state, often resulting in the conversion of alcohols to carboxylic acids. In this synthesis, the primary alcohol (PhCH2CH2OH) can be oxidized to a carboxylic acid (PhCH2CH2COOH) using oxidizing agents such as potassium permanganate (KMnO4) or chromium trioxide (CrO3). Understanding the conditions and reagents for effective oxidation is crucial for this transformation.

Reagents and Solvents

The choice of reagents and solvents is critical in organic synthesis as they influence the reaction pathway, yield, and selectivity. For the oxidation of the alcohol to a carboxylic acid, selecting an appropriate oxidizing agent and solvent (like water or an alcohol) can enhance the reaction efficiency. Familiarity with common reagents and their properties is essential for successful synthesis.

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another, which is a fundamental concept in organic chemistry. In this case, converting a primary alcohol to a carboxylic acid exemplifies this concept. Understanding the mechanisms and conditions that facilitate these conversions is vital for planning multistep syntheses effectively.

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Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

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Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(c)

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(d)

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(a) Why?

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Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

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Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.(a) PhCH2CH2OH → PhCH2CH2COOH

Key Concepts

Oxidation Reactions

Reagents and Solvents

Functional Group Interconversion

Watch next

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.
(a) PhCH₂CH₂OH → PhCH₂CH₂COOH